(2-benzenesulfonyl-1-vinyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[c,d]azulen-8-yl)dimethylamine

Base Information

• Chemical Name: (2-benzenesulfonyl-1-vinyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[c,d]azulen-8-yl)dimethylamine
• CAS No.: 405893-10-9
• Molecular Formula: C₂₁H₂₂N₂O₃S
• Molecular Weight: 382.483
• Mol file: 405893-10-9.mol

Synonyms:(2-benzenesulfonyl-1-vinyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[c,d]azulen-8-yl)dimethylamine

Chemical Property of (2-benzenesulfonyl-1-vinyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[c,d]azulen-8-yl)dimethylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2-benzenesulfonyl-1-vinyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[c,d]azulen-8-yl)dimethylamine

There total 12 articles about (2-benzenesulfonyl-1-vinyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[c,d]azulen-8-yl)dimethylamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

(2-Benzenesulfonyl-1-iodo-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]azulen-8-yl)dimethylamine + tri-n-butyl(vinyl)tin (7486-35-3) → (2-benzenesulfonyl-1-vinyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[c,d]azulen-8-yl)dimethylamine (405893-10-9)

Guidance literature:

With lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In DMF (N,N-dimethyl-formamide); at 100 ℃; for 3h;

Reference yield:

4-Hydroxyindole-3-carbaldehyde (81779-27-3) → (2-benzenesulfonyl-1-vinyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[c,d]azulen-8-yl)dimethylamine (405893-10-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: dmap / acetonitrile / 3 h / 0 °C

2.1: sodium hydride / tetrahydrofuran / 19 h / 0 °C

3.1: sodium hydroxide / tetrahydrofuran; water / 1 h

3.2: 3 h / 50 °C

4.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C

4.2: 4 h / 0 °C

5.1: 1,4-dioxane / 0.33 h / Heating / reflux

6.1: hydrogenchloride / 1,4-dioxane; water / 0.33 h / Heating / reflux

7.1: sodium tris(acetoxy)borohydride; acetic acid / tetrahydrofuran / 1 h / 20 °C

8.1: n-butyllithium / tetrahydrofuran; hexane; chloroform / 2 h / -70 - -30 °C

8.2: -70 - 20 °C

9.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / -70 °C

9.2: 2 h / -70 °C

9.3: 2 h / -70 °C

10.1: lithium chloride / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / DMF (N,N-dimethyl-formamide) / 3 h / 100 °C

With hydrogenchloride; dmap; sodium hydroxide; n-butyllithium; chloroformic acid ethyl ester; sodium tris(acetoxy)borohydride; sodium hydride; acetic acid; triethylamine; diisopropylamine; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; DMF (N,N-dimethyl-formamide); hexane; chloroform; water; acetonitrile;

Reference yield:

3-Formyl-4-hydroxyindole-1-carboxylic acid tert-butyl ester (404888-00-2) → (2-benzenesulfonyl-1-vinyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[c,d]azulen-8-yl)dimethylamine (405893-10-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 1,4-diaza-bicyclo[2.2.2]octane / 24 h / 4 °C

2.1: pyridine; acetic anhydride / 1 h / 0 °C

2.2: 6 h / 80 °C

3.1: sodium hydroxide / tetrahydrofuran; water / 1 h

3.2: 3 h / 50 °C

4.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / 0 °C

4.2: 4 h / 0 °C

5.1: 1,4-dioxane / 0.33 h / Heating / reflux

6.1: hydrogenchloride / 1,4-dioxane; water / 0.33 h / Heating / reflux

7.1: sodium tris(acetoxy)borohydride; acetic acid / tetrahydrofuran / 1 h / 20 °C

8.1: n-butyllithium / tetrahydrofuran; hexane; chloroform / 2 h / -70 - -30 °C

8.2: -70 - 20 °C

9.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / -70 °C

9.2: 2 h / -70 °C

9.3: 2 h / -70 °C

10.1: lithium chloride / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / DMF (N,N-dimethyl-formamide) / 3 h / 100 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; sodium hydroxide; n-butyllithium; chloroformic acid ethyl ester; acetic anhydride; sodium tris(acetoxy)borohydride; acetic acid; triethylamine; diisopropylamine; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; DMF (N,N-dimethyl-formamide); hexane; chloroform; water;

upstream raw materials:

tri-n-butyl(vinyl)tin

1H-indol-4-ol

(2-benzenesulfonyl-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[c,d]azulen-8-yl)dimethylamine

7H-6-oxa-2-azabenzo[c,d]azulene-2,8-dicarboxylic acid 2-tert-butyl ester 8-methyl ester

Refernces

• 1、 -. "TRICYCLIC INDOLE COMPOUNDS HAVING AFFINITY FOR SEROTONIN RECEPTOR". . . Retrieved 2008/06/13.